Rondebosch Boys' School was originally known as Rondebosch High School for Junior Boys and came into being in the latter part of the 19th century following the initiative of the Dutch Reformed Church representative of the district, the Rev Bernard Marchand.

The first headmaster, Robert Ramage (aged 38) took up this position on 1 February 1897 with the school having just 8 pupils from Standards 2 - 7. Faced with a flush of applications from local residents, two further developments occurred: a junior department was opened and a one-acre plot of ground, "The Firs", at the corner of Campground and Rouwkoop Roads was purchased for £1900.

New school buildings were erected and teaching commenced there in September 1898. Two years later Mr Ramage bought a local property which had been named Canigou Estate after an imposing monastery located high in the Pyrenees. This became a much needed school hostel.

The school flourished and, by 1927, had an enrollment of 568 boys. The Preparatory School's first headmaster, Mr WH "Papa" Law (1930-1943) was a Yorkshireman who was previously head of the large Tembuland Teachers' Training College where Nelson Mandela once studied.

He was followed by Mr JCR Enslin (1943-1966) who had very definite ideas on education and who guided the school through its change of site in 1948. The next incumbent was Mr RD Holmes (1967-1972), a quiet, sincere man who remained at the helm until his appointment to the inspectorate. He was succeeded by former staff member Mr DM Laidlaw (1972-1987), an ex-RAF pilot, whose innovations included a science room, a computer centre and a 'Magnet' class for extending the brighter senior pupils.

Mr Bruce Lane (1987-1997), the fifth headmaster, proved to be a dynamic educator and administrator. He oversaw the major renovations which were completed in 1994. He served the school with distinction, especially during its hectic centenary year in 1997.

Mr Tony Ryan, formerly deputy of Rondebosch Boys' High (and Pretoria Boys' High School), is the present headmaster. Since his appointment he has displayed commendable inter-personal skills and dedication. The school is undoubtedly in good hands as it continues to prepare boys for a successful future as it develops their spiritual, academic, emotional and social skills.